It is definitely interesting what is happening and I could some see landlord and real estate applications coming soon if this keeps rolling.

There's tons of options and even free options for landlords. 95+% of ours pay online and we have 3 tenants that drop payments off at our office.

However, I should note that this tenant has been late paying rent several times recently, which has added some strain to the landlord-tenant relationship.How would you approach this situation?

Maybe you don't want to be a landlord or own property? 

Tired landlords and conventional loans weren't available.   

How should this be handled: tenant pays, landlord pays or split costs and why?

All of my landlords we have using Azibo and they all seem to like it and haven't had complaints in over two years from them or from the tenants.

We have a 14-page management contract that we've added our real experiences to over the years, with the intent of protecting both us AND the landlord.

I explained to the landlord what my business plan was, and paid him a set rent amount each month (though slightly higher than market rate rent).

If anything there might be a discount b/c there are so many landlords who want this option so that they don't have long term tenants in the building so they have the option to sell the place vacant.